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Iridium, [N-[(1R,2R)-2-(amino-κN)cyclohexyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-, stereoisomer; Iridium, [N-[(1R,2R)-2-(amino-κN)cyclohexyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-)-1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-; Iridium, [N-[(1S,2S)-2-(amino-κN)cyclohexyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-, stereoisomer

  1. Takao Ikariya

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01597

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Ikariya, T. 2013. Iridium, [N-[(1R,2R)-2-(amino-κN)cyclohexyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-, stereoisomer; Iridium, [N-[(1R,2R)-2-(amino-κN)cyclohexyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-)-1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-; Iridium, [N-[(1S,2S)-2-(amino-κN)cyclohexyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-, stereoisomer. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. Tokyo Institute of Technology, Tokyo, Japan

Publication History

  1. Published Online: 16 SEP 2013

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Abstract

(1R,2R)-isomer

[223247-70-9] C23H34ClIrN2O2S (MW 630.24)

(1S,2S)-isomer

(catalyst precursors for asymmetric transfer hydrogenation/hydrogenation of ketones and imines and aerobic oxidation of alcohols)

Physical Data: mp 208 °C (dec.); d 1.620 g cm−3.

Solubility: soluble in CH2Cl2, CHCl3, THF, acetonitrile, and 2-propanol.

Form Supplied in: yellow solid; not available commercially.

Analysis of Reagent Purity: purity is analyzed by 1H NMR (CD2Cl2): δ 0.81-2.61 (m, 10H, C6H10), 1.66 (s, 15H, C5(CH3)5), 2.36 (s, 3H, CH3C6H4SO2), 3.52 (br, 1H, NHH), 3.82 (br, 1H, NHH), 3.97 (br, 1H, NHH), 7.18 (d, 2H, C6H4), 7.95 (d, 2H, C6H4).

Preparative Method: by treatment of (1R,2R)-N-(p-toluenesulfonyl)cyclohexane-1,2-diamine (Commercially available from Aldrich) with [Cp*Ir(μ-Cl)Cl]2 in the presence of triethylamine in CH2Cl2 under an inert gas atmosphere (eq 1). The reaction mixture was extracted three times with water. The organic layer was dried with MgSO4 and filtered through filter paper. Reprecipitation by addition of hexane to the filtrate gave the product as a yellow solid.

original image(1)

Purification: recrystallization by slow diffusion of diethyl ether into a CH2Cl2 solution.

Handling, Storage, and Precautions: the complex can be handled in air, but it is recommended to be stored under a dry inert gas atmosphere for prolonged storage.

Featured Compounds

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  1. 1 - 36
Compound Information
Molecular Weight:796.698
Molecular Formula:C20H30Cl4Ir2
InChIKey:LPFQDSLPQTYADR-UHFFFAOYSA-J
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:HORBZNNRSXNJKD-LDYMZIIASA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:HORBZNNRSXNJKD-KWQFWETISA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:CREVFIPIRJCEIY-QMMMGPOBSA-N
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Compound Information
Molecular Weight:599.75
Molecular Formula:C31H34N2O2RuS
InChIKey:CPZIADVWRUNNBT-LGPFPQHZSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.3062
Molecular Formula:C14H20O4
InChIKey:UCRAJZOMPJEEHD-RKPOYUIDSA-N
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Compound Information
Molecular Weight:250.2903
Molecular Formula:C14H18O4
InChIKey:WCRWHUOIGFAUSQ-XEVMNIDFSA-N
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Compound Information
Molecular Weight:691.904
Molecular Formula:C31H35IrN2O2S
InChIKey:QCIYTWZBKARJOW-OXIQQVKJSA-N
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Compound Information
Molecular Weight:112.212
Molecular Formula:C4H9KO
InChIKey:LPNYRYFBWFDTMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:310.3869
Molecular Formula:C20H22O3
InChIKey:ODHHTIYRUDURPW-QBVIUOPJSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:WAPNOHKVXSQRPX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:WAPNOHKVXSQRPX-SSDOTTSWSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:KWOLFJPFCHCOCG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:615.808
Molecular Formula:C25H31IrN2O2S
InChIKey:UCTZYGIGFZDEHM-WVFPUEBHSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:630.263
Molecular Formula:C23H34ClIrN2O2S
InChIKey:WBQXMSSCDQUOMU-SQWZUNHGSA-M
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Compound Information
Molecular Weight:209.2863
Molecular Formula:C15H15N
InChIKey:JATCPLSBWDXCNE-SSZFMOIBSA-N
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Compound Information
Molecular Weight:211.3022
Molecular Formula:C15H17N
InChIKey:ZYZHMSJNPCYUTB-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:211.3022
Molecular Formula:C15H17N
InChIKey:ZYZHMSJNPCYUTB-CYBMUJFWSA-N
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Compound Information
Molecular Weight:630.263
Molecular Formula:C23H34ClIrN2O2S
InChIKey:WBQXMSSCDQUOMU-GPWCTTBFSA-M
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Compound Information
Molecular Weight:343.62
Molecular Formula:AgF6Sb
InChIKey:GSXFODUDOAXUBF-UHFFFAOYSA-H
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Compound Information
Molecular Weight:60.095
Molecular Formula:C3H8O
InChIKey:KFZMGEQAYNKOFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:870.6
Molecular Formula:C25H36F6IrN3O2SSb
InChIKey:NVVLCKNNCIVJBG-UYYRLJAOSA-H
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:188.1465
Molecular Formula:C9H7F3O
InChIKey:ABXGMGUHGLQMAW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.1624
Molecular Formula:C9H9F3O
InChIKey:YNVXCOKNHXMBQC-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:190.1624
Molecular Formula:C9H9F3O
InChIKey:YNVXCOKNHXMBQC-LURJTMIESA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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